1-Piperidinecarboxaldehyde → (2,2'-Bipyridine)-6-carbaldehyde

HRID 594241

Reaktionsgleichung

Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1.[Li]CCCC.N1([CH:25]=[O:26])CCCCC1.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[N:7]1[C:2]([CH:25]=[O:26])=[CH:3][CH:4]=[CH:5][C:6]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

A cooled (−78° C.) solution of commercially available 6-bromo-2,2′-bipyridine (600 mg; 2.55 mmol) in anh. THF (10 ml) was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.60 ml; 2.56 mmol), and the resulting mixture was further stirred at −78° C., under nitrogen, for 30 min. Piperidine-1-carbaldehyde (577 mg; 5.10 mmol) was added dropwise to the cooled (−78° C.) reaction mixture, and stirring was continued at −78° C. for 30 min. Aq. sat. NH4Cl (25 ml) and AcOEt (50 ml) were added, and the separated organic layer was further washed with brine (20 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (toluene/AcOEt=8/2) afforded [2,2′-bipyridine]-6-carbaldehyde as a dark-purple solid. LC-MS (conditions C): tR=0.75 min.; [M+H]+: 185.24 g/mol.

Aufarbeitung

temperaturecooled
custom(−78° C.) reaction mixture
stirringstirring
waitwas continued at −78° C. for 30 min
washthe separated organic layer was further washed with brine (20 ml)
dry with materialdried over anh. MgSO4
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure
customPurification by FC (toluene/AcOEt=8/2)

Quellen und Nachweise

ORD-Eintrag: ord-e0ed0a106cb047a5beecfe728ba245f3
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09242970B2

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